JPWO2019240058A1 - Fullerene compounds, lubricants for magnetic recording media and magnetic recording media - Google Patents
Fullerene compounds, lubricants for magnetic recording media and magnetic recording media Download PDFInfo
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- JPWO2019240058A1 JPWO2019240058A1 JP2020525542A JP2020525542A JPWO2019240058A1 JP WO2019240058 A1 JPWO2019240058 A1 JP WO2019240058A1 JP 2020525542 A JP2020525542 A JP 2020525542A JP 2020525542 A JP2020525542 A JP 2020525542A JP WO2019240058 A1 JPWO2019240058 A1 JP WO2019240058A1
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- fullerene
- compound
- bronsted
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 239000000314 lubricant Substances 0.000 title claims abstract description 41
- 229910003472 fullerene Inorganic materials 0.000 claims abstract description 72
- -1 fullerene compound Chemical class 0.000 claims abstract description 57
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 39
- 239000007848 Bronsted acid Substances 0.000 claims abstract description 35
- 239000002608 ionic liquid Substances 0.000 claims abstract description 35
- 239000003341 Bronsted base Substances 0.000 claims abstract description 32
- 239000010410 layer Substances 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 67
- 239000011241 protective layer Substances 0.000 claims description 31
- 230000001050 lubricating effect Effects 0.000 claims description 29
- 239000000758 substrate Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000002430 hydrocarbons Chemical group 0.000 claims description 16
- 239000010702 perfluoropolyether Substances 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 8
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
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- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 9
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- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
- G11B5/62—Record carriers characterised by the selection of the material
- G11B5/72—Protective coatings, e.g. anti-static or antifriction
- G11B5/725—Protective coatings, e.g. anti-static or antifriction containing a lubricant, e.g. organic compounds
- G11B5/7253—Fluorocarbon lubricant
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract
フラーレン化合物、それを含む磁気記録媒体用潤滑剤、および磁気記録媒体を提供する。本発明のフラーレン化合物は、下記一般式(1)で示される、ブレンステッド酸(Hn1X)とブレンステッド塩基([(R2R3)N−]m1−R1)から形成されるイオン液体であり、前記ブレンステッド酸またはブレンステッド塩基のどちらか一方にフラーレンを有する基を含有し、もう一方にパーフルオロアルキル鎖を含有することを特徴とするフラーレン化合物。[化1]Provided are a fullerene compound, a lubricant for a magnetic recording medium containing the fullerene compound, and a magnetic recording medium. The fullerene compound of the present invention is an ionic liquid formed from a Bronsted acid (Hn1X) and a Bronsted base ([(R2R3) N-] m1-R1) represented by the following general formula (1), and is the Bronsted acid. A fullerene compound comprising a group having a fullerene in either a steady acid or a Bronsted base and a perfluoroalkyl chain in the other. [Chemical 1]
Description
本発明は、フラーレン化合物、磁気記録媒体用潤滑剤及び磁気記録媒体に関する。
本願は、2018年6月12日に、日本に出願された特願2018−111894号に基づき優先権を主張し、その内容をここに援用する。The present invention relates to a fullerene compound, a lubricant for a magnetic recording medium, and a magnetic recording medium.
The present application claims priority based on Japanese Patent Application No. 2018-111894 filed in Japan on June 12, 2018, the contents of which are incorporated herein by reference.
近年、磁気記録媒体の記録容量を向上させる方式として、HAMR(Heat Assisted Magnetic Recording)が開発されている。このHAMR方式は、近接場光により局所的に加熱し、熱オフセットをかけながら磁場の記録・再生をする次世代記録技術である。この技術を利用することにより、微弱な信号でも周りの熱ノイズの影響を受けなくなり、信頼性を保つことができる。しかし、このHAMR方式は、近接場光にて加熱するため、潤滑剤にさらなる耐熱性・繰り返し耐久性が求められる。具体的には、250℃以上の耐熱性が求められる。また、このような環境下であっても、磁気記録媒体装置の高信頼性を実現させるためには、繰り返し摺動しても優れた潤滑性を維持できる潤滑膜を設計することが重要である。 In recent years, HAMR (Heat Assisted Magnetic Recording) has been developed as a method for improving the recording capacity of a magnetic recording medium. This HAMR method is a next-generation recording technology that records and reproduces a magnetic field while locally heating it with near-field light and applying heat offset. By using this technology, even a weak signal is not affected by the surrounding thermal noise, and reliability can be maintained. However, since this HAMR method heats with near-field light, the lubricant is required to have further heat resistance and repeatability. Specifically, heat resistance of 250 ° C. or higher is required. Further, even in such an environment, in order to realize high reliability of the magnetic recording medium device, it is important to design a lubricating film that can maintain excellent lubricity even if it slides repeatedly. ..
このような要求に対し、耐熱性の優れた材料を用いる提案や、イオン液体の利用を提案している特許が見られる。
例えば、特許文献1には、末端にカルボキシル基を有するパーフルオロポリエーテルとジアミンの化合物が開示されている。優れた潤滑作用、耐久性が開示されている。
また、特許文献2には、パーフルオロポリエーテル骨格を有するスルホン酸またはカルボン酸と、炭素数が2〜5の無置換のアルキレン基を介して窒素原子に結合したパーフルオロアルキル鎖を有するアミンとから形成されるイオン液体を含有する潤滑剤が開示されている。優れた耐熱性、潤滑性(低い摩擦係数)が開示されている。
また、特許文献3には、フラーレン骨格およびパーフルオロポリエーテル鎖を有するフラーレン誘導体を含む潤滑剤が開示されている。優れた被覆性が開示されている。In response to such demands, there are patents proposing the use of materials with excellent heat resistance and the use of ionic liquids.
For example,
Further,
Further,
しかしながら、これらの先行技術では、HAMR方式のような次世代記録技術においては、十分な耐熱性及び潤滑性が得られない。 However, with these prior arts, sufficient heat resistance and lubricity cannot be obtained in the next-generation recording technology such as the HAMR method.
本発明は、上記状況を鑑みてなされたものであり、HAMR方式のような次世代記録技術においても、十分な耐熱性及び潤滑性が実現できる磁気記録媒体用潤滑剤の材料として、好適に用いることが出来るフラーレン化合物を提供することを目的とする。また、本発明は、本発明のフラーレン化合物を含む磁気記録媒体用潤滑剤を有する磁気記録媒体を提供することを目的とする。 The present invention has been made in view of the above circumstances, and is suitably used as a material for a lubricant for a magnetic recording medium capable of achieving sufficient heat resistance and lubricity even in a next-generation recording technology such as the HAMR method. It is an object of the present invention to provide a fullerene compound capable of providing a capable fullerene compound. Another object of the present invention is to provide a magnetic recording medium having a lubricant for a magnetic recording medium containing the fullerene compound of the present invention.
本件発明者は、鋭意検討を行った結果、ブレンステッド酸またはブレンステッド塩基のどちらか一方にフラーレンを有する基を含有するイオン液体化合物が有望であることを見出した。 As a result of diligent studies, the present inventor has found that an ionic liquid compound containing a group having a fullerene in either a Bronsted acid or a Bronsted base is promising.
すなわち本発明は以下の事項に関する。
[1] 下記一般式(1)で示される、ブレンステッド酸(Hn1X)とブレンステッド塩基([(R2R3)N−]m1−R1)から形成されるイオン液体であり、
前記ブレンステッド酸またはブレンステッド塩基のどちらか一方にフラーレンを有する基を含有し、もう一方にパーフルオロアルキル鎖を含有することを特徴とするフラーレン化合物。That is, the present invention relates to the following matters.
[1] An ionic liquid formed from a Bronsted acid (H n1 X) and a Bronsted base ([(R 2 R 3 ) N-] m1- R 1 ) represented by the following general formula (1).
A fullerene compound characterized in that either one of the Bronsted acid or the Bronsted base contains a group having a fullerene, and the other contains a perfluoroalkyl chain.
(式中、R1、R2、R3のうち少なくとも1つは炭素数が1〜20の炭化水素基であり;X、R1、R2、R3のうち少なくとも1つはフラーレン骨格を有し、X、R1、R2、R3のうち少なくとも1つはパーフルオロアルキル鎖を有する。R2、R3は互いに結合し、含窒素複素環を形成しても良い。n1、n2、m1、m2は1〜6の整数であり、かつ、n1×n2=m1×m2である。)
[2] 前記ブレンステッド酸が、分子内にフラーレン骨格と、スルホン酸基またはカルボン酸基とを有し、前記ブレンステッド塩基がパーフルオロポリエーテル鎖を有する[1]に記載のフラーレン化合物。
[3] 前記ブレンステッド酸が、分子内にパーフルオロポリエーテル鎖と、スルホン酸基またはカルボン酸基とを有し、前記ブレンステッド塩基がフラーレン骨格を有する[1]に記載のフラーレン化合物。
[4] 前記ブレンステッド酸が下記式(6)、(7)又は(8)で示される化合物であり、
前記ブレンステッド塩基が下記式(10)又は(11)で示される化合物である[1]又は[2]に記載のフラーレン化合物。(In the formula, at least one of R 1 , R 2 , R 3 is a hydrocarbon group having 1 to 20 carbon atoms; at least one of X, R 1 , R 2 , R 3 has a fullerene skeleton. At least one of X, R 1 , R 2 , and R 3 has a perfluoroalkyl chain. R 2 and R 3 may be bonded to each other to form a nitrogen-containing heterocycle. N 1 , n 2 , m 1 , and m 2 are integers of 1 to 6 and n 1 × n 2 = m 1 × m 2. )
[2] The fullerene compound according to [1], wherein the Bronsted acid has a fullerene skeleton and a sulfonic acid group or a carboxylic acid group in the molecule, and the Bronsted base has a perfluoropolyether chain.
[3] The fullerene compound according to [1], wherein the Bronsted acid has a perfluoropolyether chain and a sulfonic acid group or a carboxylic acid group in the molecule, and the Bronsted base has a fullerene skeleton.
[4] The Bronsted acid is a compound represented by the following formula (6), (7) or (8).
The fullerene compound according to [1] or [2], wherein the Bronsted base is a compound represented by the following formula (10) or (11).
Cn(OH)x−y(OSO3H)y(6)
式中、Cnはポリ水酸化フラーレン硫酸水素エステルの母体であるフラーレンを示し、xは10〜30の範囲の数であり、yは5〜10の範囲の数である。CnはC60、C70、C76、C78、C80、C82、C84から選ばれる少なくとも1種である。C n (OH) xy (OSO 3 H) y (6)
In the formula, C n represents fullerene, which is the base of polyhydroxide fullerene hydrogen sulfate ester, x is a number in the range of 10 to 30, and y is a number in the range of 5 to 10. C n is at least one selected from C 60, C 70, C 76 , C 78, C 80, C 82, C 84.
NH2(CH2CH2O)pCH2CF2−(OCF2CF2)m(OCF2)n−OCF2CH2(OCH2CH2)qNH2 (10)
式中p、qは1〜3である。mは1〜30であり、nは0〜30である。NH 2 (CH 2 CH 2 O) p CH 2 CF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 CH 2 (OCH 2 CH 2 ) q NH 2 (10)
In the formula, p and q are 1-3. m is 1 to 30, and n is 0 to 30.
CF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2OCH2CH2NH2 (11)CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 CH 2 OCH 2 CH 2 NH 2 (11)
[5] 前記ブレンステッド酸が下記式(12)〜(15)のいずれかで示される化合物であり、前記ブレンステッド塩基が下記式(16)で示される化合物である[1]又は[3]に記載のフラーレン化合物。 [5] The Bronsted acid is a compound represented by any of the following formulas (12) to (15), and the Bronsted base is a compound represented by the following formula (16) [1] or [3]. The fullerene compound described in.
HO3S(CH2)3OCH2CF2−(OCF2CF2)m(OCF2)n−OCF2CH2O(CH2)3SO3H (12)
式中、mは1〜30であり、nは0〜30である。HO 3 S (CH 2 ) 3 OCH 2 CF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 CH 2 O (CH 2 ) 3 SO 3 H (12)
In the formula, m is 1 to 30 and n is 0 to 30.
CF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2O(CH2)3SO3H (13)CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 CH 2 O (CH 2 ) 3 SO 3 H (13)
HOOCCF2−(OCF2CF2)m(OCF2)n−OCF2COOH (14)
式中、mは1〜30であり、nは0〜30である。HOOCCF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 COOH (14)
In the formula, m is 1 to 30 and n is 0 to 30.
CF3CF2CF2CF2−(OCF2CF2)2−OCF2COOH (15)CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 COOH (15)
[6] 前記イオン液体の熱分解温度が、300℃以上である[1]〜[5]のいずれかに記載のフラーレン化合物。
[7] 数平均分子量が500〜20000の範囲内にある[1]〜[6]のいずれかに記載にフラーレン化合物。
[8] [1]〜[7]のいずれかに記載のフラーレン化合物を含むことを特徴とする磁気記録媒体用潤滑剤。
[9] 基板上に、少なくとも磁性層と保護層と潤滑層が順次設けられた磁気記録媒体であって、前記潤滑層は、[1]〜[7]のいずれかに記載のフラーレン化合物を含むことを特徴とする磁気記録媒体。
[10] 前記潤滑層の平均膜厚が0.5nm〜2.5nmである[9]に記載の磁気記録媒体。[6] The fullerene compound according to any one of [1] to [5], wherein the thermal decomposition temperature of the ionic liquid is 300 ° C. or higher.
[7] The fullerene compound according to any one of [1] to [6], which has a number average molecular weight in the range of 500 to 20000.
[8] A lubricant for a magnetic recording medium, which comprises the fullerene compound according to any one of [1] to [7].
[9] A magnetic recording medium in which at least a magnetic layer, a protective layer, and a lubricating layer are sequentially provided on a substrate, and the lubricating layer contains the fullerene compound according to any one of [1] to [7]. A magnetic recording medium characterized by that.
[10] The magnetic recording medium according to [9], wherein the average film thickness of the lubricating layer is 0.5 nm to 2.5 nm.
本発明によれば、潤滑剤の蒸発や熱分解といった熱的な安定性を改善し、かつ優れた潤滑特性を長期に亘り維持させることができる。また、この潤滑剤を磁気記録媒体に用いることより,高信頼性を有する磁気記録媒体、特にHAMR方式でも高信頼性を有する磁気記録媒体を提供できる。 According to the present invention, it is possible to improve thermal stability such as evaporation and thermal decomposition of the lubricant, and to maintain excellent lubricating characteristics for a long period of time. Further, by using this lubricant as a magnetic recording medium, it is possible to provide a magnetic recording medium having high reliability, particularly a magnetic recording medium having high reliability even in the HAMR method.
以下、本発明の実施の形態について、詳細に説明する。
本発明の化合物は、下記式(1)で表される。本発明の化合物は、ブレンステッド酸(Hn1X)とブレンステッド塩基([(R2R3)N−]m1−R1)から形成されるイオン液体である。前記ブレンステッド酸またはブレンステッド塩基のどちらか一方にフラーレンを有する基を含有し、もう一方にパーフルオロアルキル鎖を含有することを特徴とするフラーレン化合物である。Hereinafter, embodiments of the present invention will be described in detail.
The compound of the present invention is represented by the following formula (1). The compound of the present invention is an ionic liquid formed from a Bronsted acid (H n1 X) and a Bronsted base ([(R 2 R 3 ) N-] m1- R 1). It is a fullerene compound characterized by containing a group having a fullerene in either the Bronsted acid or the Bronsted base and containing a perfluoroalkyl chain in the other.
一般式(1)中、R1、R2、R3のうち少なくとも1つは炭素数が1〜20の炭化水素基であり;X、R1、R2、R3のうち少なくとも1つはフラーレン骨格を有し、X、R1、R2、R3のうち少なくとも1つはパーフルオロアルキル鎖を有する。R2、R3は互いに結合し、含窒素複素環を形成しても良い。n1、n2、m1、m2は1〜6の整数であり、かつ、n1×n2=m1×m2である。In general formula (1), at least one of R 1 , R 2 , R 3 is a hydrocarbon group having 1 to 20 carbon atoms; at least one of X, R 1 , R 2 , R 3 is. It has a fullerene skeleton and at least one of X, R 1 , R 2 , and R 3 has a perfluoroalkyl chain. R 2 and R 3 may be bonded to each other to form a nitrogen-containing heterocycle. n 1 , n 2 , m 1 , and m 2 are integers of 1 to 6, and n 1 × n 2 = m 1 × m 2 .
本発明の炭素数が1〜20の炭化水素基として、炭素数が1〜20のアルキル基、アルケニル基、アリール基、アラルキル基が挙げられる。R2、R3は互いに結合し、含窒素複素環を形成しても良い。Examples of the hydrocarbon group having 1 to 20 carbon atoms in the present invention include an alkyl group having 1 to 20 carbon atoms, an alkenyl group, an aryl group and an aralkyl group. R 2 and R 3 may be bonded to each other to form a nitrogen-containing heterocycle.
m1が2〜6の整数である場合、R1はm1個の結合部位を有する炭化水素基である。前記炭化水素基はフラーレン骨格又はパーフルオロアルキル鎖を有することが好ましい。R2、R3はそれぞれ独立して、水素原子又は炭素数が1〜20の炭化水素基であることが好ましい。前記炭素数が1〜20の炭化水素基が置換基を有しても良い。If m 1 is an integer of 2-6, then R 1 is a hydrocarbon group with m 1 binding sites. The hydrocarbon group preferably has a fullerene skeleton or a perfluoroalkyl chain. It is preferable that R 2 and R 3 are independently hydrogen atoms or hydrocarbon groups having 1 to 20 carbon atoms. The hydrocarbon group having 1 to 20 carbon atoms may have a substituent.
[フラーレン骨格]
本発明のフラーレン骨格として、炭素数60から120のフラーレン、あるいはこれらの2量体または3量体等を挙げることができる。より具体的にはC60、C70、C76、C78、C82、C84、C90、C94、C96が挙げられる。これらの中で溶解性の観点から好ましいのはC60、C70である。[Fullerene skeleton]
Examples of the fullerene skeleton of the present invention include fullerenes having 60 to 120 carbon atoms, dimers or trimers thereof, and the like. More specifically, C 60 , C 70 , C 76 , C 78 , C 82 , C 84 , C 90 , C 94 , and C 96 can be mentioned. Of these, C 60 and C 70 are preferable from the viewpoint of solubility.
[パーフルオロアルキル鎖]
本発明のパーフルオロアルキル鎖は、炭素数1〜30のパーフルオロアルキル鎖であることが好ましい。
本発明のパーフルオロアルキル鎖は、途中にエーテル結合を有しても良い。例えば、パーフルオロメチレンオキシド重合体、パーフルオロエチレンオキシド重合体、パーフルオロ−n−プロピレンオキシド重合体、パーフルオロイソプロピレンオキシド重合体、これらの共重合体などを挙げることができる。パーフルオロアルキルの分子量は、特に限定されないが、500〜10000が好ましく、1000〜5000であることが特に好ましい。
本発明のパーフルオロアルキル鎖としては、以下の構造が好適に用いられる。[Perfluoroalkyl chain]
The perfluoroalkyl chain of the present invention is preferably a perfluoroalkyl chain having 1 to 30 carbon atoms.
The perfluoroalkyl chain of the present invention may have an ether bond in the middle. For example, a perfluoromethylene oxide polymer, a perfluoroethylene oxide polymer, a perfluoro-n-propylene oxide polymer, a perfluoroisopropylene oxide polymer, a copolymer thereof, and the like can be mentioned. The molecular weight of perfluoroalkyl is not particularly limited, but is preferably 500 to 10000, and particularly preferably 1000 to 5000.
The following structure is preferably used as the perfluoroalkyl chain of the present invention.
−CF2−(OCF2CF2)b−(OCF2)c−OCF2− (2)-CF 2- (OCF 2 CF 2 ) b- (OCF 2 ) c -OCF 2- (2)
−CF(CF3)−(OCF(CF3)CF2)d−OCF(CF3)− (3)-CF (CF 3 )-(OCF (CF 3 ) CF 2 ) d -OCF (CF 3 )-(3)
−CF2CF2−(OCF2CF2CF2)e−OCF2CF2− (4)−CF 2 CF 2- (OCF 2 CF 2 CF 2 ) e −OCF 2 CF 2- (4)
CF3CF2CF2CF2(OCF2CF2)2−OCF2CH2− (5)CF 3 CF 2 CF 2 CF 2 (OCF 2 CF 2 ) 2- OCF 2 CH 2- (5)
式(2)、式(3)、式(4)中のb、d、eはそれぞれ1〜30の整数を表し、cは0〜30の整数を表す。 In equations (2), (3), and (4), b, d, and e each represent an integer of 1 to 30, and c represents an integer of 0 to 30.
含フッ素エーテル化合物の数平均分子量(Mn)は、ブルカー・バイオスピン社製AVANCEIII400による1H−NMRおよび19F−NMRによって測定された値である。具体的には、19F−NMRによって測定された積分値よりPFPE鎖の繰り返し単位数を算出し、数平均分子量を求めた。
NMR溶媒は、d−アセトン、d−テトラヒドロフラン、d−トルエン、ヘキサフルオロベンゼンの単独または混合溶媒を用いた。The number average molecular weight (Mn) of the fluorine-containing ether compound is a value measured by 1 H-NMR and 19 F-NMR by AVANCE III400 manufactured by Bruker Biospin. Specifically, the number of repeating units of the PFPE chain was calculated from the integrated value measured by 19 F-NMR, and the number average molecular weight was obtained.
As the NMR solvent, a single solvent or a mixed solvent of d-acetone, d-tetrahydrofuran, d-toluene and hexafluorobenzene was used.
[イオン液体]
本発明のイオン液体とは、例えば、フラーレン骨格を有するカルボン酸とパーフルオロアルキル鎖を有するアミン、フラーレン骨格を有するスルホン酸とパーフルオロアルキル鎖を有するアミン、パーフルオロアルキル鎖を有するカルボン酸とフラーレン骨格を有するアミン、パーフルオロアルキル鎖を有するスルホン酸とフラーレン骨格を有するアミンから形成される。これらのうち、フラーレン骨格を有するカルボン酸とパーフルオロアルキル鎖を有するアミンの組み合わせは、合成が容易である点から好ましい。[Ionic liquid]
The ionic liquid of the present invention includes, for example, a carboxylic acid having a fullerene skeleton and an amine having a perfluoroalkyl chain, a sulfonic acid having a fullerene skeleton and an amine having a perfluoroalkyl chain, and a carboxylic acid and a fullerene having a perfluoroalkyl chain. It is formed from an amine having a skeleton, a sulfonic acid having a perfluoroalkyl chain, and an amine having a fullerene skeleton. Of these, a combination of a carboxylic acid having a fullerene skeleton and an amine having a perfluoroalkyl chain is preferable from the viewpoint of easy synthesis.
十分な潤滑性を得るためには、フラーレン1分子に対し、パーフルオロアルキル鎖は2本以上あることが望ましい。例えば、カルボン酸が2つ以上結合したフラーレン骨格を有する基とパーフルオロアルキル鎖を有するアミンから形成されるイオン液体が望ましい。パーフルオロアルキル鎖が2本以上であると潤滑性と耐熱性が両立できる。 In order to obtain sufficient lubricity, it is desirable that there are two or more perfluoroalkyl chains per molecule of fullerene. For example, an ionic liquid formed from a group having a fullerene skeleton in which two or more carboxylic acids are bonded and an amine having a perfluoroalkyl chain is desirable. When the number of perfluoroalkyl chains is two or more, both lubricity and heat resistance can be achieved.
本発明のフラーレン化合物の数平均分子量が500〜10000の範囲内にあることが好ましく、1000〜5000の範囲内にあることがより好ましい。 The number average molecular weight of the fullerene compound of the present invention is preferably in the range of 500 to 10000, and more preferably in the range of 1000 to 5000.
(第1の実施形態)
[フラーレン化合物]
本発明の第1の実施形態のフラーレン化合物は、下記一般式(1)で示される、ブレンステッド酸(Hn1X)とブレンステッド塩基([(R2R3)N−]m1−R1)から形成されるイオン液体であり、前記ブレンステッド酸(Hn1X)にフラーレンを有する基を含有し、ブレンステッド塩基([(R2R3)N−]m1−R1)にパーフルオロアルキル鎖を含有することを特徴とする。(First Embodiment)
[Fullerene compound]
The fullerene compound of the first embodiment of the present invention is a Bronsted acid (H n1 X) and a Bronsted base ([(R 2 R 3 ) N-] m1- R 1] represented by the following general formula (1). ) and ionic liquid formed from, (containing a group having a fullerene H n1 X), Bronsted base (the Bronsted acid [(R 2 R 3) N- ] m1 -R 1) in perfluoro It is characterized by containing an alkyl chain.
一般式(1)中、R1、R2、R3のうち少なくとも1つは炭素数が1〜20の炭化水素基であり;Xはフラーレン骨格を有し、R1、R2、R3のうち少なくとも1つはパーフルオロアルキル鎖を有する。R2、R3は互いに結合し、含窒素複素環を形成しても良い。n1、n2、m1、m2は1〜6の整数であり、かつ、n1×n2=m1×m2である。In general formula (1), at least one of R 1 , R 2 , and R 3 is a hydrocarbon group having 1 to 20 carbon atoms; X has a fullerene skeleton and R 1 , R 2 , R 3 At least one of them has a perfluoroalkyl chain. R 2 and R 3 may be bonded to each other to form a nitrogen-containing heterocycle. n 1 , n 2 , m 1 , and m 2 are integers of 1 to 6, and n 1 × n 2 = m 1 × m 2 .
フラーレン骨格がC60、C70であることが好ましい。The fullerene skeleton is preferably C 60 and C 70.
n1が2〜6の整数であり、n2が1であることが好ましい。n1が2〜4の整数であり、n2が1であることがより好ましい。n1が2以上であると潤滑性と耐熱性が両立できる。It is preferable that n 1 is an integer of 2 to 6 and n 2 is 1. It is more preferable that n 1 is an integer of 2 to 4 and n 2 is 1. When n 1 is 2 or more, both lubricity and heat resistance can be achieved.
m1が1、2であり、m2が1〜6であり、かつ、n1×n2=m1×m2であることが好ましい。m1が1、2であり、m2が1〜4であり、かつ、n1×n2=m1×m2であることがより好ましい。It is preferable that m 1 is 1 and 2 ,
m1が2〜6の整数である場合、R1はm1個の結合部位を有する炭素数が1〜20の炭化水素基である。前記炭素数が1〜20の炭化水素基がパーフルオロアルキル鎖を有することが好ましい。R2、R3はそれぞれ独立して、水素原子又は炭素数が1〜20の炭化水素基であることが好ましい。R2、R3は水素原子であることがより好ましい。When m 1 is an integer of 2 to 6, R 1 is a hydrocarbon group having m 1 binding site and having 1 to 20 carbon atoms. It is preferable that the hydrocarbon group having 1 to 20 carbon atoms has a perfluoroalkyl chain. It is preferable that R 2 and R 3 are independently hydrogen atoms or hydrocarbon groups having 1 to 20 carbon atoms. It is more preferable that R 2 and R 3 are hydrogen atoms.
[ブレンステッド酸]
本実施形態にかかるブレンステッド酸としては、フラーレン骨格を有するスルホン酸、フラーレン骨格を有するカルボン酸等が挙げられる。
フラーレン骨格を有するスルホン酸は、例えば、フラーレンと発煙硫酸から、特開2005−8564記載の方法で合成できる。
具体的構造は、例えば以下の式(6)で示される化合物6である。[Bronsted acid]
Examples of the Bronsted acid according to the present embodiment include a sulfonic acid having a fullerene skeleton, a carboxylic acid having a fullerene skeleton, and the like.
The sulfonic acid having a fullerene skeleton can be synthesized from, for example, fullerene and fuming sulfuric acid by the method described in JP-A-2005-8564.
The specific structure is, for example, compound 6 represented by the following formula (6).
Cn(OH)x−y(OSO3H)y(6)
式中、Cnはポリ水酸化フラーレン硫酸水素エステルの母体であるフラーレンを示し、xは10〜30の範囲の数であり、yは5〜10の範囲の数である。CnはC60、C70、C76、C78、C80、C82、C84等から選ばれる少なくとも1種である。C n (OH) xy (OSO 3 H) y (6)
In the formula, C n represents fullerene, which is the base of polyhydroxide fullerene hydrogen sulfate ester, x is a number in the range of 10 to 30, and y is a number in the range of 5 to 10. C n is at least one selected from C 60, C 70, C 76 , C 78, C 80, C 82, C 84 , etc..
上記の式(6)で示される化合物6は以下の式(6A)で示される化合物6Aであることが好ましい。 The compound 6 represented by the above formula (6) is preferably the compound 6A represented by the following formula (6A).
式中、xは10〜30の範囲の数であり、yは5〜10の範囲の数である。xは10、yは5であることが好ましい。 In the formula, x is a number in the range 10-30 and y is a number in the range 5-10. It is preferable that x is 10 and y is 5.
フラーレン骨格を有するカルボン酸は、例えば、フェニルC61−ブチリックアシッド メチルエステルの加水分解物、ビス−フェニルC61−ブチリックアシッド メチルエステルの加水分解物(式(7)で示される化合物7)、フェニルC71−ブチリックアシッド メチルエステルの加水分解物などが好適に用いられる。また、フラーレンを、N―メチルグリシン、およびアルデヒド(式(9)で示される化合物9)と反応させることにより得られる化合物の加水分解物(式(8)で示される化合物8)も好適に用いられる。The carboxylic acid having a fullerene skeleton is, for example, a hydrolyzate of phenyl C 61 -butyric acid methyl ester and a hydrolyzate of bis-phenyl C 61 -butyric acid methyl ester (compound 7 represented by the formula (7)). , A hydrolyzate of phenyl C 71 -butyric acid methyl ester and the like are preferably used. Further, a hydrolyzate of a compound obtained by reacting fullerene with N-methylglycine and an aldehyde (compound 9 represented by the formula (9)) (compound 8 represented by the formula (8)) is also preferably used. Be done.
[ブレンステッド塩基]
本実施形態のブレンステッド塩基としては、例えば、パーフルオロアルキル鎖を有するアミンが挙げられる。
パーフルオロアルキル鎖を有するアミンは、例えば、パーフルオロアルキル鎖を有するアルコールの水酸基をトシル化した後に、得られるトシル基をフタルイミド化し、更に得られるイミド基をアミノ化することにより得ることができる。
具体的構造は、例えば以下の式(10)で示される化合物10及び式(11)で示される化合物11である。[Bronsted bases]
Examples of the Bronsted base of the present embodiment include amines having a perfluoroalkyl chain.
The amine having a perfluoroalkyl chain can be obtained, for example, by tosylating the hydroxyl group of an alcohol having a perfluoroalkyl chain, phthalimidizing the obtained tosyl group, and further amifying the obtained imide group.
Specific structures are, for example, the compound 10 represented by the following formula (10) and the
NH2(CH2CH2O)pCH2CF2−(OCF2CF2)m(OCF2)n−OCF2CH2(OCH2CH2)qNH2 (10)
式中p、qは1〜3である。mは1〜30であり、nは0〜30である。
p、qは0であるとアミノ基のpKbが低下し好ましくない。また4以上であると分子量が大きくなり好ましくない。NH 2 (CH 2 CH 2 O) p CH 2 CF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 CH 2 (OCH 2 CH 2 ) q NH 2 (10)
In the formula, p and q are 1-3. m is 1 to 30, and n is 0 to 30.
When p and q are 0, the pKb of the amino group decreases, which is not preferable. Further, when it is 4 or more, the molecular weight becomes large, which is not preferable.
CF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2OCH2CH2NH2 (11)CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 CH 2 OCH 2 CH 2 NH 2 (11)
[フラーレン化合物の具体例]
以下に、本実施形態に係るフラーレン化合物の例示化合物を挙げるが、本発明はこれらの化合物には限定されない。[Specific examples of fullerene compounds]
Hereinafter, exemplary compounds of the fullerene compound according to the present embodiment will be listed, but the present invention is not limited to these compounds.
本実施形態に係る上記一般式(1)で示されるフラーレン化合物の具体例は、表1に示す。 Specific examples of the fullerene compound represented by the above general formula (1) according to the present embodiment are shown in Table 1.
式(A)で示される化合物Aは、化合物7と化合物10から形成されるイオン液体である。
式中、pとqは1であり、mとnは10である。Compound A represented by the formula (A) is an ionic liquid formed from compound 7 and compound 10.
In the formula, p and q are 1, and m and n are 10.
式(B)で示される化合物Bは、化合物7と化合物11から形成されるイオン液体である。
Compound B represented by the formula (B) is an ionic liquid formed from compound 7 and
式(C)で示される化合物Cは、化合物8と化合物10から形成されるイオン液体である。
式中、pとqは1であり、mとnは10である。Compound C represented by the formula (C) is an ionic liquid formed from compound 8 and compound 10.
In the formula, p and q are 1, and m and n are 10.
式(D)で示される化合物Dは、化合物8と化合物11から形成されるイオン液体である。
Compound D represented by the formula (D) is an ionic liquid formed from compound 8 and
式(G)で示される化合物Gは、化合物6Aと化合物11から形成されるイオン液体である。
式中、xは10、yは5である。Compound G represented by the formula (G) is an ionic liquid formed from compound 6A and
In the formula, x is 10 and y is 5.
(フラーレン化合物(イオン液体)の合成法)
次に、本実施の形態に係るイオン液体の合成法について説明する。イオン液体は、ブレンステッド酸とブレンステッド塩基とから合成される。例えば、フラーレン骨格を有するカルボン酸とパーフルオロポリエーテルを主骨格とするアミンとを当量混合して中和することによって得られる。(Synthesis method of fullerene compound (ionic liquid))
Next, a method for synthesizing the ionic liquid according to the present embodiment will be described. Ionic liquids are synthesized from Bronsted acids and Bronsted bases. For example, it is obtained by mixing an equivalent amount of a carboxylic acid having a fullerene skeleton and an amine having a perfluoropolyether as a main skeleton and neutralizing them.
(イオン液体の効果)
一般的にフラーレン化合物は有機溶媒に溶けづらく、フラーレン骨格にパーフルオロポリエーテル鎖を導入することは容易ではない。本発明の方法によると、例えば、合成容易なカルボキシル基を有するフラーレンとアミノ基を有するパーフルオロポリエーテル鎖からイオン液体を合成することで、比較的容易にフラーレン骨格にパーフルオロポリエーテル鎖を導入することが可能である。(Effect of ionic liquid)
In general, fullerene compounds are difficult to dissolve in organic solvents, and it is not easy to introduce a perfluoropolyether chain into the fullerene skeleton. According to the method of the present invention, for example, a perfluoropolyether chain can be introduced into a fullerene skeleton relatively easily by synthesizing an ionic liquid from a fullerene having a carboxyl group and a perfluoropolyether chain having an amino group, which are easy to synthesize. It is possible to do.
(潤滑剤)
本発明の潤滑剤は、前述のイオン液体を含むことを特徴とする。本発明の一形態の潤滑剤は、前述のイオン液体を単独で使用してもよいが、従来公知の潤滑剤と組み合わせて用いてもよい。例えば、本発明の一形態の潤滑剤は、長鎖カルボン酸、長鎖カルボン酸エステル、パーフルオロアルキルカルボン酸エステル、カルボン酸パーフルオロアルキルエステル、パーフルオロアルキルカルボン酸パーフルオロアルキルエステル、パーフルオロポリエーテル誘導体などと組み合わせて使用することが可能である。(lubricant)
The lubricant of the present invention is characterized by containing the above-mentioned ionic liquid. As the lubricant of one embodiment of the present invention, the above-mentioned ionic liquid may be used alone, or may be used in combination with a conventionally known lubricant. For example, the lubricant of one embodiment of the present invention includes long-chain carboxylic acid, long-chain carboxylic acid ester, perfluoroalkylcarboxylic acid ester, carboxylic acid perfluoroalkyl ester, perfluoroalkylcarboxylic acid perfluoroalkyl ester, and perfluoropoly. It can be used in combination with an ether derivative or the like.
また、厳しい条件で潤滑効果を持続させるために、重量比30:70〜70:30程度の配合比で極圧剤を併用してもよい。極圧剤は、境界潤滑領域において部分的に金属接触が生じたときに、これに伴う摩擦熱によって金属面と反応し、反応生成物被膜を形成することにより、摩擦・摩耗防止作用を行うものである。極圧剤としては、リン系極圧剤、イオウ系極圧剤、ハロゲン系極圧剤、有機金属系極圧剤、複合型極圧剤などのいずれも使用できる。 Further, in order to maintain the lubricating effect under severe conditions, an extreme pressure agent may be used in combination at a blending ratio of about 30:70 to 70:30 by weight. Extreme pressure agents act to prevent friction and wear by forming a reaction product film by reacting with the metal surface due to the frictional heat that accompanies partial metal contact in the boundary lubrication region. Is. As the extreme pressure agent, any of a phosphorus-based extreme pressure agent, a sulfur-based extreme pressure agent, a halogen-based extreme pressure agent, an organometallic extreme pressure agent, a composite type extreme pressure agent, and the like can be used.
また、必要に応じて防錆剤を併用してもよい。防錆剤としては、通常この種の磁気記録媒体の防錆剤として使用可能であるものであれば良く、例えばフェノール類、ナフトール類、キノン類、窒素原子を含む複素環化合物、酸素原子を含む複素環化合物、硫黄原子を含む複素環化合物などが挙げられる。また、防錆剤は、潤滑剤として混合して用いても良いが、非磁性支持体上に磁性層を形成し、その上部に防錆剤層を塗布した後、潤滑剤層を塗布するというように、2層以上に分けて積層しても良い。 In addition, a rust preventive may be used in combination if necessary. The rust preventive may be any one that can be usually used as a rust preventive for this type of magnetic recording medium, and includes, for example, phenols, naphthols, quinones, a heterocyclic compound containing a nitrogen atom, and an oxygen atom. Examples thereof include heterocyclic compounds and heterocyclic compounds containing a sulfur atom. Further, the rust preventive may be mixed and used as a lubricant, but a magnetic layer is formed on the non-magnetic support, the rust preventive layer is applied on the upper portion, and then the lubricant layer is applied. As described above, it may be divided into two or more layers and laminated.
また、潤滑剤の溶媒としては、イソプロピルアルコール(IPA)、エタノール等のアルコール系溶媒やフッ素系溶剤などから単独又は組み合わせて使用することができる。 Further, as the solvent of the lubricant, an alcohol solvent such as isopropyl alcohol (IPA) or ethanol, a fluorine solvent, or the like can be used alone or in combination.
本発明に係る潤滑剤の分子量は特に制約はされないが、例えば数平均分子量(Mn)が、500〜20000の範囲であることが好ましく、1000〜10000の範囲であることが更に好ましい。適度な粘度による修復性を備え、好適な潤滑性能を発揮し、しかも優れた耐熱性を兼ね備えることができるからである。 The molecular weight of the lubricant according to the present invention is not particularly limited, but for example, the number average molecular weight (Mn) is preferably in the range of 500 to 20000, and more preferably in the range of 1000 to 10000. This is because it has repairability due to an appropriate viscosity, exhibits suitable lubrication performance, and has excellent heat resistance.
本発明に係る潤滑剤を適当な方法で分子量分画することにより、分子量分散度(重量平均分子量(Mw)/数平均分子量(Mn)比)を1.3以下とするのが好ましい。
本発明において、分子量分画する方法に特に制限を設ける必要は無いが、例えば、シリカゲルカラムクロマトグラフィーやゲルパーミエーションクロマトグラフィー(GPC)法による分子量分画、超臨界抽出法による分子量分画などを用いることができる。It is preferable that the molecular weight dispersion (weight average molecular weight (Mw) / number average molecular weight (Mn) ratio) is 1.3 or less by fractionating the molecular weight of the lubricant according to the present invention by an appropriate method.
In the present invention, it is not necessary to particularly limit the method for molecular weight fractionation, but for example, molecular weight fractionation by silica gel column chromatography, gel permeation chromatography (GPC) method, molecular weight fractionation by supercritical extraction method, etc. Can be used.
(潤滑層)
本発明に係る潤滑剤を用いて潤滑層を成膜するにあたっては、潤滑剤を適当な溶媒に分散又は溶解させた溶液を用いて、例えばディップ法により塗布して成膜することができる。溶媒としては、イオン液体の構造にも依るが、例えばフッ素系溶媒(三井デュポンフロロケミカル社製商品名バートレル(登録商標)XFなど)を好ましく用いることができる。潤滑層の成膜方法はもちろん上記ディップ法には限らず、スピンコート法、スプレイ法、ペーパーコート法などの成膜方法を用いてもよい。(Lubrication layer)
When forming a lubricating layer using the lubricant according to the present invention, a solution in which the lubricating agent is dispersed or dissolved in an appropriate solvent can be used, for example, by a dip method to form a film. As the solvent, for example, a fluorine-based solvent (trade name Bertrel (registered trademark) XF manufactured by Mitsui DuPont Fluorochemical Co., Ltd.) can be preferably used, although it depends on the structure of the ionic liquid. Of course, the film forming method of the lubricating layer is not limited to the above dip method, and a film forming method such as a spin coating method, a spray method, or a paper coating method may be used.
本発明においては、潤滑層の成膜後に、磁気記録媒体に熱処理を施すことが好ましい。この熱処理を施すことにより、潤滑層と保護層との密着性を向上させ、付着力を向上させることができるので、本発明にとって好適である。熱処理温度は80〜180℃とすることが好ましい。この温度が80℃未満では、密着作用が十分ではなく、一方、180℃を超えると、潤滑剤が熱分解する場合があるので好ましくない。また、熱処理時間は5〜120分とすると好適である。また、本発明においては、成膜した潤滑層の保護層への付着力をより向上させるために、上記熱処理前、もしくは熱処理後に磁気記録媒体をUV照射処理してもよい。 In the present invention, it is preferable to heat-treat the magnetic recording medium after forming the lubricating layer. By performing this heat treatment, the adhesion between the lubricating layer and the protective layer can be improved and the adhesive force can be improved, which is suitable for the present invention. The heat treatment temperature is preferably 80 to 180 ° C. If this temperature is less than 80 ° C., the adhesion is not sufficient, while if it exceeds 180 ° C., the lubricant may thermally decompose, which is not preferable. The heat treatment time is preferably 5 to 120 minutes. Further, in the present invention, in order to further improve the adhesive force of the formed lubricating layer to the protective layer, the magnetic recording medium may be subjected to UV irradiation treatment before or after the heat treatment.
本発明にあっては、潤滑層の膜厚は、5〜25Åとするのがよい。5Å未満では、潤滑層としての潤滑性能が低下する場合がある。また25Åを超えると、薄膜化の観点から好ましくない。 In the present invention, the thickness of the lubricating layer is preferably 5 to 25 Å. If it is less than 5 Å, the lubrication performance as a lubricating layer may deteriorate. Further, if it exceeds 25 Å, it is not preferable from the viewpoint of thinning.
(保護層)
また、本発明における保護層としては、炭素系保護層を好ましく用いることができる。特にアモルファス炭素保護層が好ましい。保護層はとくに炭素系保護層であることにより、本発明に係る潤滑剤のフラーレンと保護層との相互作用が一層高まり、本発明による作用効果がより一層発揮されるため好ましい。なお、炭素系保護層と潤滑層の付着力を調節するために、炭素系保護層を水素化炭素及び/又は窒素化炭素として、水素及び/又は窒素の含有量を調節することが可能である。この場合、水素の含有量は水素前方散乱法(HFS)で測定したときに3〜20原子%とするのが好ましい。また、窒素の含有量はX線光電子分光分析法(XPS)で測定したときに、4〜15原子%とするのが好ましい。
本発明における炭素系保護層においては、水素及び/又は窒素は保護層全体に均一に含有される必要はなく、とくに保護層の潤滑層側に窒素を含有させ、磁性層側に水素を含有させた組成傾斜層とすることが好適である。(Protective layer)
Further, as the protective layer in the present invention, a carbon-based protective layer can be preferably used. An amorphous carbon protective layer is particularly preferable. Since the protective layer is particularly a carbon-based protective layer, the interaction between the fullerene of the lubricant according to the present invention and the protective layer is further enhanced, and the action and effect according to the present invention are further exerted, which is preferable. In order to adjust the adhesive force between the carbon-based protective layer and the lubricating layer, it is possible to adjust the content of hydrogen and / or nitrogen by using the carbon-based protective layer as carbon hydride and / or carbon nitrogen. .. In this case, the hydrogen content is preferably 3 to 20 atomic% as measured by the hydrogen forward scattering method (HFS). The nitrogen content is preferably 4 to 15 atomic% when measured by X-ray photoelectron spectroscopy (XPS).
In the carbon-based protective layer of the present invention, hydrogen and / or nitrogen need not be uniformly contained in the entire protective layer, and in particular, nitrogen is contained in the lubricating layer side of the protective layer and hydrogen is contained in the magnetic layer side. It is preferable to use a graded layer with a different composition.
本発明において炭素系保護層を用いる場合は、例えばDCマグネトロンスパッタリング法により成膜することができる。特にプラズマCVD法により成膜されたアモルファス炭素保護層とすることが好ましい。プラズマCVD法により成膜することで保護層表面が均一となり密に成膜される。従って、より粗さが小さい、CVD法で成膜された保護層上に本発明による潤滑層を形成することは好ましい。
本発明にあっては、保護層の膜厚は、10〜70Åとするのがよい。10Å未満では、保護層としての性能が低下する場合がある。また70Åを超えると、薄膜化の観点から好ましくない。When a carbon-based protective layer is used in the present invention, a film can be formed by, for example, a DC magnetron sputtering method. In particular, it is preferable to use an amorphous carbon protective layer formed by a plasma CVD method. By forming a film by the plasma CVD method, the surface of the protective layer becomes uniform and the film is densely formed. Therefore, it is preferable to form the lubricating layer according to the present invention on the protective layer formed by the CVD method, which has a smaller roughness.
In the present invention, the film thickness of the protective layer is preferably 10 to 70 Å. If it is less than 10 Å, the performance as a protective layer may deteriorate. Further, if it exceeds 70 Å, it is not preferable from the viewpoint of thinning.
(磁気記録媒体)
本発明の磁気記録媒体においては、基板はガラス基板またはアルミ基板であることが好ましい。ガラス基板は剛性があり、平滑性に優れるので、高記録密度化には好適である。ガラス基板としては、例えばアルミノシリケートガラス基板が挙げられ、特に化学強化されたアルミノシリケートガラス基板が好適である。(Magnetic recording medium)
In the magnetic recording medium of the present invention, the substrate is preferably a glass substrate or an aluminum substrate. Since the glass substrate has rigidity and excellent smoothness, it is suitable for increasing the recording density. Examples of the glass substrate include an aluminosilicate glass substrate, and a chemically strengthened aluminosilicate glass substrate is particularly suitable.
本発明においては、上記基板の主表面の粗さは、Rmaxが6nm以下、Raが0.6nm以下の超平滑であることが好ましい。なお、ここでいう表面粗さRmax、Raは、JIS B0601の規定に基づくものである。
本発明の磁気記録媒体は、基板上に少なくとも磁性層と保護層と本発明に係る潤滑剤を含む潤滑層とを備えている。本発明において、上記磁性層は特に制限はなく、面内記録方式用磁性層であっても、垂直記録方式用磁性層であってもよい。In the present invention, the roughness of the main surface of the substrate, R max is 6nm or less, it is preferred that R a is less ultra-smooth 0.6 nm. Herein, the term surface roughness R max, R a is based on the provisions of JIS B0601.
The magnetic recording medium of the present invention includes at least a magnetic layer, a protective layer, and a lubricating layer containing the lubricant according to the present invention on a substrate. In the present invention, the magnetic layer is not particularly limited, and may be a magnetic layer for in-plane recording method or a magnetic layer for perpendicular recording method.
本発明の磁気記録媒体においては、基板と磁性層との間に、必要に応じて下地層を設けることができる。また、該下地層と基板との間に付着層や軟磁性層等を設けることもできる。この場合、上記下地層としては、例えば、Cr層、Ta層、Ru層、あるいはCrMo,CoW,CrW,CrV,CrTi合金層などが挙げられ、上記付着層としては、例えば、CrTi,NiAl,AlRu合金層などが挙げられる。また、上記軟磁性層としては、例えばCoZrTa合金膜などが挙げられる。 In the magnetic recording medium of the present invention, a base layer can be provided between the substrate and the magnetic layer, if necessary. Further, an adhesive layer, a soft magnetic layer, or the like can be provided between the base layer and the substrate. In this case, examples of the base layer include Cr layer, Ta layer, Ru layer, CrMo, CoW, CrW, CrV, CrTi alloy layer and the like, and examples of the adhesion layer include CrTi, NiAl and AlRu. An alloy layer and the like can be mentioned. Further, examples of the soft magnetic layer include a CoZrTa alloy film and the like.
本発明の磁気記録媒体は、特にLUL(Load Unload)方式の磁気記録媒体装置に搭載される磁気記録媒体として好適である。LUL方式の導入に伴う磁気ヘッド浮上量の一段の低下により、10nm以下の低浮上量においても磁気記録媒体が安定して動作することが求められるようになってきており、低浮上量のもとで高い信頼性を有する本発明の磁気記録媒体は好適である。 The magnetic recording medium of the present invention is particularly suitable as a magnetic recording medium mounted on a LUL (Load Unload) type magnetic recording medium device. Due to the further decrease in the amount of levitation of the magnetic head accompanying the introduction of the LUL method, it has become necessary for the magnetic recording medium to operate stably even at a low levitation amount of 10 nm or less. The magnetic recording medium of the present invention having high reliability is suitable.
(第2の実施形態)
第2の実施形態では、第1の実施形態と異なる構成に関わる部分のみについて主に説明する。
[フラーレン化合物]
本発明の第2の実施形態のフラーレン化合物は、上記一般式(1)で示される、ブレンステッド酸(Hn1X)とブレンステッド塩基([(R2R3)N−]m1−R1)から形成されるイオン液体であり、前記ブレンステッド酸(Hn1X)にパーフルオロアルキル鎖を含有し、ブレンステッド塩基(R2−N(R3)−R1)にフラーレンを有する基を含有することを特徴とする。(Second embodiment)
In the second embodiment, only the part related to the configuration different from that of the first embodiment will be mainly described.
[Fullerene compound]
Fullerene compounds of the second embodiment of the present invention is represented by the general formula (1), Bronsted acids (H n1 X) and Bronsted base ([(R 2 R 3) N-] m1 -R 1 ) and ionic liquid formed from, a group having the Bronsted acid (in H n1 X) containing perfluoroalkyl chain, Bronsted base (R 2 -N (R 3) -R 1) to the fullerene It is characterized by containing.
一般式(1)中、R1、R2、R3のうち少なくとも1つは炭素数が1〜20の炭化水素基であり;Xはパーフルオロアルキル鎖を有し、R1、R2、R3のうち少なくとも1つはフラーレン骨格を有する。R2、R3は互いに結合し、含窒素複素環を形成しても良い。n1、n2、m1、m2は1〜6の整数であり、かつ、n1×n2=m1×m2である。In general formula (1), at least one of R 1 , R 2 , R 3 is a hydrocarbon group having 1 to 20 carbon atoms; X has a perfluoroalkyl chain, R 1 , R 2 , ,. At least one of R 3 has a fullerene skeleton. R 2 and R 3 may be bonded to each other to form a nitrogen-containing heterocycle. n 1 , n 2 , m 1 , and m 2 are integers of 1 to 6, and n 1 × n 2 = m 1 × m 2 .
フラーレン骨格がC60、C70であることが好ましい。The fullerene skeleton is preferably C 60 and C 70.
n1が1、2であり、n2が1〜6であり、かつ、n1×n2=m1×m2であることが好ましい。n1が1、2であり、n2が1〜4であり、かつ、n1×n2=m1×m2であることがより好ましい。It is preferable that n 1 is 1 and 2 ,
m1が2〜6の整数であり、m2が1であることが好ましい。m1が2〜4の整数であり、m2が1であることがより好ましい。m1が2以上であると潤滑性と耐熱性が両立できる。It is preferable that m 1 is an integer of 2 to 6 and m 2 is 1. It is more preferable that m 1 is an integer of 2 to 4 and m 2 is 1. When m 1 is 2 or more, both lubricity and heat resistance can be achieved.
m1が2〜6の整数である場合、R1はm1個の結合部位を有する炭化水素基である。前記炭化水素基が置換基を有してもよい。前記炭化水素基がフラーレン骨格を有することが好ましい。If m 1 is an integer of 2-6, then R 1 is a hydrocarbon group with m 1 binding sites. The hydrocarbon group may have a substituent. It is preferable that the hydrocarbon group has a fullerene skeleton.
[ブレンステッド酸]
本実施形態のブレンステッド酸としては、例えば、パーフルオロアルキル鎖を有するスルホン酸、パーフルオロアルキル鎖を有するカルボン酸などが挙げられる。[Bronsted acid]
Examples of the Bronsted acid of the present embodiment include a sulfonic acid having a perfluoroalkyl chain and a carboxylic acid having a perfluoroalkyl chain.
パーフルオロアルキル鎖を有するスルホン酸は、例えば、上記構造式(2)〜(5)の骨格を有する化合物の末端にスルホン酸基(−SO3H)を有する。この場合、原料として、ソルベイソレクシス社製Fomblin(登録商標)Z−DOL(構造式:HOCH2CF2(OCF2CF2)m(OCF2)n−OCF2−CH2OHやCF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2OH)等を用いて、例えば特開2016−9509に記載の方法で合成される。
具体的構造は、例えば、式(12)で示される化合物12又は式(13)で示される化合物13であるが、これらに限定されるものではない。Sulfonic acid having a perfluoroalkyl chains have, for example, the structural formula (2) to terminal sulfonic acid group of a compound having a skeleton of (5) (-
The specific structure is, for example, compound 12 represented by the formula (12) or compound 13 represented by the formula (13), but is not limited thereto.
HO3S(CH2)3OCH2CF2−(OCF2CF2)m(OCF2)n−OCF2CH2O(CH2)3SO3H (12)
式中、mは1〜30であり、nは0〜30である。HO 3 S (CH 2 ) 3 OCH 2 CF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 CH 2 O (CH 2 ) 3 SO 3 H (12)
In the formula, m is 1 to 30 and n is 0 to 30.
CF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2O(CH2)3SO3H (13)CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 CH 2 O (CH 2 ) 3 SO 3 H (13)
パーフルオロアルキル鎖を有するカルボン酸は、炭素数1〜20のパーフルオロアルキル鎖の末端にカルボン酸を有するもので、例えば、ウンデカフルオロヘキサノイックアシッド、ヘプタデカフルオロノナノイックアシッド、トリコサフルオロドデカノイックアシッドなどが挙げられる。また、原料として、ソルベイソレクシス社製Fomblin Z−DOL(構造式:HOCH2CF2(OCF2CF2)m(OCF2)n−OCF2−CH2OHやCF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2OH)等を用いて、合成される。
また、パーフルオロアルキル鎖を有するカルボン酸は、市販品であっても良い。市販品としては、例えば、ソルベイソレクシス社製のFomblin Z−DIAC(数平均分子量、約2,000)(式14)、Fomblin Z−DIAC4000(数平均分子量、約4,000)、Fluorolink(登録商標)C10(数平均分子量、約1,700)、パーフルオロ−3,6,9−トリオキサデカノイックアシッド(式15)などが挙げられる。
具体的構造は、例えば式(14)で示される化合物14又は式(15)で示される化合物15であるが、これらに限定されるものではない。The carboxylic acid having a perfluoroalkyl chain has a carboxylic acid at the end of the perfluoroalkyl chain having 1 to 20 carbon atoms, for example, undecafluorohexanoic acid, heptadecafluorononanoic acid, tricosafluoro. Dodecanoic acid and the like can be mentioned. In addition, as a raw material, Fomblin Z-DOL (structural formula: HOCH 2 CF 2 (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2- CH 2 OH and CF 3 CF 2 CF 2 CF 2 manufactured by Solvaisolexis Co., Ltd. - using (OCF 2 CF 2) 2 -OCF 2
Further, the carboxylic acid having a perfluoroalkyl chain may be a commercially available product. Examples of commercially available products include Fomblin Z-DIAC (number average molecular weight, about 2,000) (formula 14), Fomblin Z-DIAC4000 (number average molecular weight, about 4,000), Fluorlink (registered) manufactured by Solvaisolexis. Trademarks) C10 (number average molecular weight, about 1,700), perfluoro-3,6,9-trioxadecanoic acid (formula 15) and the like can be mentioned.
The specific structure is, for example, compound 14 represented by the formula (14) or compound 15 represented by the formula (15), but is not limited thereto.
HOOCCF2−(OCF2CF2)m(OCF2)n−OCF2COOH (14)
式中、mは1〜30であり、nは0〜30である。HOOCCF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 COOH (14)
In the formula, m is 1 to 30 and n is 0 to 30.
CF3CF2CF2CF2−(OCF2CF2)2−OCF2COOH (15)CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 COOH (15)
また、本実施形態において、パーフルオロアルキル鎖を有するカルボン酸またはスルホン酸は、上記構造式(2)〜(4)の骨格の中でも、構造式(3)の骨格を有することが好ましい。構造式(3)は、ソルベイソレクシス社製Fomblin Z−DOL(構造式:HOCH2CF2−(OCF2CF2)m(OCF2)n−OCF2CH2OH)、ソルベイソレクシス社製Fomblin Z−DIAC(構造式:HOOCCF2−(OCF2CF2)m(OCF2)n−OCF2COOH)等の優れた潤滑性を示す化合物と主骨格が同じであるため、優れた潤滑性を得ることができる。Further, in the present embodiment, the carboxylic acid or sulfonic acid having a perfluoroalkyl chain preferably has the skeleton of the structural formula (3) among the skeletons of the above structural formulas (2) to (4). The structural formula (3) is Fomblin Z-DOL manufactured by Sorbet Lubrication Co., Ltd. (Structural formula: HOCH 2 CF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 CH 2 OH), manufactured by Sorbet Lubrication Co., Ltd. Excellent lubricity because the main skeleton is the same as that of compounds showing excellent lubricity such as Fomblin Z-DIAC (structural formula: HOOCCF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 COOH). Can be obtained.
[ブレンステッド塩基]
本実施形態のブレンステッド塩基としては、例えば、フラーレン骨格を有するアミンなどが挙げられる。
フラーレン骨格を有するアミンは、例えば、式(16)で示される、フロンティアカーボン社のJ204(化合物16)などが好適に用いられる。[Bronsted bases]
Examples of the Bronsted base of the present embodiment include amines having a fullerene skeleton.
As the amine having a fullerene skeleton, for example, J204 (Compound 16) of Frontier Carbon Co., Ltd. represented by the formula (16) is preferably used.
[フラーレン化合物の具体例]
以下に、本実施形態に係るフラーレン化合物の例示化合物を挙げるが、本発明はこれらの化合物には限定されない。[Specific examples of fullerene compounds]
Hereinafter, exemplary compounds of the fullerene compound according to the present embodiment will be listed, but the present invention is not limited to these compounds.
本実施形態に係る上記一般式(1)で示されるフラーレン化合物の具体例は、表2に示す。 Specific examples of the fullerene compound represented by the above general formula (1) according to the present embodiment are shown in Table 2.
式(E)で示される化合物Eは、化合物16と化合物13から形成されるイオン液体である。 Compound E represented by the formula (E) is an ionic liquid formed from compound 16 and compound 13.
式(F)で示される化合物Fは、化合物16と化合物15から形成されるイオン液体である。 Compound F represented by the formula (F) is an ionic liquid formed from compound 16 and compound 15.
また、イオン液体の熱分解温度は、250℃以上であることが好ましく、300℃以上であることがより好ましい。350℃以上であることが更に好ましい。イオン液体の熱分解温度が250℃以上であることにより、例えばHAMR方式の記録時の加熱にも潤滑性を維持することができる。 The thermal decomposition temperature of the ionic liquid is preferably 250 ° C. or higher, more preferably 300 ° C. or higher. It is more preferably 350 ° C. or higher. When the thermal decomposition temperature of the ionic liquid is 250 ° C. or higher, lubricity can be maintained even during heating during recording by, for example, the HAMR method.
以下、本発明を実施例に基づいて具体的に説明する。なお、本発明はこれらの実施例にのみ限定されるものではない。 Hereinafter, the present invention will be specifically described based on examples. The present invention is not limited to these examples.
(合成例1)
<化合物6Aの合成>
フロンティアカーボン社製C60を原料として用いて、特開2005−8564記載の方法で、本発明のブレンステッド酸として、以下の式(6A)で示される化合物6Aを合成した。(Synthesis Example 1)
<Synthesis of compound 6A>
Using C60 manufactured by Frontier Carbon Co., Ltd. as a raw material, the compound 6A represented by the following formula (6A) was synthesized as the Bronsted acid of the present invention by the method described in JP-A-2005-8564.
得られた化合物6Aの元素分析結果は以下であった。
C:55.74%、H:0.78%、S:12.32%。
The elemental analysis results of the obtained compound 6A were as follows.
C: 55.74%, H: 0.78%, S: 12.32%.
(合成例2)
<化合物11の合成>
Alfa Chemistry社製1H,1H−Perfluoro−3,6,9−trioxatridecan−1−ol(構造式:CF3CF2CF2CF2−OCF2CF2−OCF2CH2OH、数平均分子量548)と2−(2−Chloroethoxy)tetrahydro−2H−pyranを反応させ、その後脱保護した化合物の水酸基をトシル化した後に、得られるトシル基をフタルイミド化し、更に得られるイミド基をアミノ化することにより、本発明のブレンステッド塩基としての化合物11を合成した。(Synthesis Example 2)
<Synthesis of
Alfa Chemistry Co. 1H, 1H-Perfluoro-3,6,9- trioxatridecan-1-ol ( Formula: CF 3 CF 2 CF 2 CF 2 -
CF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2OCH2CH2NH2 (11)CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 CH 2 OCH 2 CH 2 NH 2 (11)
(合成例3)
<化合物7の合成>
ビス−フェニルC61−ブチリックアシッド メチルエステル(フロンティアカーボン社)の加水分解物として、本発明のブレンステッド酸としての化合物7を合成した。(Synthesis Example 3)
<Synthesis of compound 7>
Compound 7 as the Bronsted acid of the present invention was synthesized as a hydrolyzate of bis-phenyl C61-butyric acid methyl ester (Frontier Carbon Co., Ltd.).
(合成例4)
<化合物8の合成>
フラーレンC60(フロンティアカーボン社)を、N―メチルグリシン、およびトリメチルベンゼントリカルボキシレートの部分還元から得られるアルデヒドと反応させることにより得られる化合物の加水分解物として、本発明のブレンステッド酸としての化合物8を合成した。(Synthesis Example 4)
<Synthesis of Compound 8>
The Bronsted acid of the present invention is used as a hydrolyzate of a compound obtained by reacting fullerene C 60 (Frontier Carbon Co., Ltd.) with an aldehyde obtained from the partial reduction of N-methylglycine and trimethylbenzene tricarboxylate. Compound 8 was synthesized.
(実施例1)
[フラーレン化合物の製造]
窒素雰囲気下、100mLナスフラスコに、本発明のブレンステッド酸としての化合物7 1.07g(Mw1072、1.0mmol)とTHF50mLを仕込み、室温で撹拌し溶解させた。この溶液に、本発明のブレンステッド塩基としての化合物11 1.77g(Mw591、3.0mmol)を投入し、室温で1時間、40℃で1時間撹拌した後、溶媒を留去した。残渣をヘプタンのデカンテーションにより、洗浄し、洗液がpH7を示すまで繰り返し上澄みを除去し、本発明の第1の実施形態のフラーレン化合物としての化合物Bを合成した。(Example 1)
[Manufacturing of fullerene compounds]
Under a nitrogen atmosphere, 1.07 g (Mw1072, 1.0 mmol) of the compound 7 as Bronsted acid of the present invention and 50 mL of THF were charged in a 100 mL eggplant flask, and the mixture was stirred and dissolved at room temperature. To this solution, 1.77 g (Mw591, 3.0 mmol) of the
[潤滑剤層形成用溶液の調製]
合成した化合物BをバートレルXF(商品名、三井デュポンフロロケミカル社製)に溶解して潤滑剤層形成用溶液とした。フラーレン化合物(潤滑剤)の濃度は0.27質量%とした。なお、化合物BのバートレルXFへの溶解度は0.36質量%であった。[Preparation of solution for forming lubricant layer]
The synthesized compound B was dissolved in Bertrel XF (trade name, manufactured by Mitsui DuPont Fluorochemical Co., Ltd.) to prepare a solution for forming a lubricant layer. The concentration of the fullerene compound (lubricant) was 0.27% by mass. The solubility of compound B in Bertrel XF was 0.36% by mass.
[磁気記録媒体の製造]
<磁性層及び保護層などの形成>
図1は、実施例1による磁気記録媒体11である。
磁気記録媒体11は、非磁性基板1上に、磁性層2、保護層3、潤滑剤層4が順次形成されてなる。
洗浄済みのガラス基板(HOYA社製、外形65mm)を、DCマグネトロンスパッタ装置(アネルバ社製C−3040)の成膜チャンバ内に収容して、到達真空度1×10−5Paとなるまで成膜チャンバ内を排気した。[Manufacturing of magnetic recording medium]
<Formation of magnetic layer and protective layer>
FIG. 1 is a
The
The cleaned glass substrate (HOYA, outer diameter 65 mm) is housed in the film formation chamber of a DC magnetron sputtering device (Anerva C-3040) until the ultimate vacuum degree is 1 × 10 -5 Pa. The inside of the membrane chamber was exhausted.
その後、このガラス基板の上に、スパッタリング法によりCrTiターゲットを用いて層厚10nmの密着層を成膜した。次いで、スパッタリング法により密着層の上に軟磁性下地層として、Co−20Fe−5Zr−5Ta{Fe含有量20原子%、Zr含有量5原子%、Ta含有量5原子%、残部Co}のターゲットを用いて100℃以下の基板温度で、層厚25nmの第1軟磁性層を成膜し、その上に層厚0.7nmのRuからなる中間層と、層厚25nmのCo−20Fe−5Zr−5Taからなる第2軟磁性層とを成膜した。 Then, an adhesion layer having a layer thickness of 10 nm was formed on the glass substrate by a sputtering method using a CrTi target. Next, a target of Co-20Fe-5Zr-5Ta {Fe content 20 atomic%, Zr content 5 atomic%, Ta content 5 atomic%, balance Co} was used as a soft magnetic base layer on the adhesion layer by a sputtering method. A first soft magnetic layer having a layer thickness of 25 nm is formed on the substrate at a substrate temperature of 100 ° C. or lower, and an intermediate layer made of Ru having a layer thickness of 0.7 nm and Co-20Fe-5Zr having a layer thickness of 25 nm are formed on the first soft magnetic layer. A second soft magnetic layer made of −5 Ta was formed.
次に、軟磁性下地層の上に、スパッタリング法によりNi−6W{W含有量6原子%、残部Ni}ターゲットを用いて、層厚5nmのシード層を成膜した。その後、シード層の上に、スパッタリング法により第1の配向制御層として、スパッタ圧力を0.8Paとして層厚10nmのRu層を成膜した。次に、第1の配向制御層上に、スパッタリング法により第2の配向制御層として、スパッタ圧力を1.5Paとして層厚10nmのRu層を成膜した。 Next, a seed layer having a layer thickness of 5 nm was formed on the soft magnetic base layer by a sputtering method using a Ni-6W {W content 6 atomic%, balance Ni} target. Then, a Ru layer having a layer thickness of 10 nm was formed on the seed layer as a first orientation control layer by a sputtering method at a sputtering pressure of 0.8 Pa. Next, a Ru layer having a layer thickness of 10 nm was formed on the first orientation control layer as a second orientation control layer by a sputtering method at a sputtering pressure of 1.5 Pa.
続いて、第2の配向制御層の上に、スパッタリング法により91(Co15Cr16Pt)−6(SiO2)−3(TiO2){Cr含有量15原子%、Pt含有量16原子%、残部Coの合金を91mol%、SiO2からなる酸化物を6mol%、TiO2からなる酸化物を3mol%}からなる第1磁性層を、スパッタ圧力を2Paとして層厚9nmで成膜した。Subsequently, on the second orientation control layer, 91 (Co15Cr16Pt) -6 (SiO 2 ) -3 (TiO 2 ) {Cr content 15 atomic%, Pt content 16 atomic%, balance Co. A first magnetic layer composed of 91 mol% of an alloy, 6 mol% of an oxide composed of SiO 2 , and 3 mol% of an oxide composed of TiO 2 } was formed at a layer thickness of 9 nm at a sputtering pressure of 2 Pa.
次に、第1磁性層の上に、スパッタリング法により88(Co30Cr)−12(TiO2){Cr含有量30原子%、残部Coの合金を88mol%、TiO2からなる酸化物を12mol%}からなる非磁性層を層厚0.3nmで成膜した。その後、非磁性層の上に、スパッタリング法により92(Co11Cr18Pt)−5(SiO2)−3(TiO2){Cr含有量11原子%、Pt含有量18原子%、残部Coの合金を92mol%、SiO2からなる酸化物を5mol%、TiO2からなる酸化物を3mol%}からなる第2磁性層を、スパッタ圧力を2Paとして層厚6nmで成膜した。Next, on the first magnetic layer, 88 (Co30Cr) -12 (TiO 2 ) {Cr content 30 atomic%, remaining Co alloy 88 mol%, TiO 2 oxide 12 mol%} by sputtering method. A non-magnetic layer made of the above was formed with a layer thickness of 0.3 nm. Then, on the non-magnetic layer, 92 (Co11Cr18Pt) -5 (SiO 2 ) -3 (TiO 2 ) {
その後、第2磁性層の上に、スパッタリング法によりRuからなる非磁性層を層厚0.3nmで成膜した。次いで、非磁性層の上に、スパッタリング法によりCo−20Cr−14Pt−3B{Cr含有量20原子%、Pt含有量14原子%、B含有量3原子%、残部Co}からなるターゲットを用いて、スパッタ圧力を0.6Paとして第3磁性層を層厚7nmで成膜した。次に、CVD法により炭素と水素からなる層厚20nmの保護層を成膜した。保護層に含まれる水素は約15原子%であった。
Then, a non-magnetic layer made of Ru was formed on the second magnetic layer by a sputtering method with a layer thickness of 0.3 nm. Then, on the non-magnetic layer, a target composed of Co-20Cr-14Pt-3B {Cr content 20 atomic%, Pt content 14 atomic%,
<潤滑層の形成>
ディップ法を用いて、保護層上に潤滑剤を塗布した。すなわち、調整された潤滑剤層形成用溶液をディップコート装置の浸漬槽に入れ、潤滑剤層形成用溶液中に、保護層までの各層が形成された基体を浸漬し、その後、浸漬槽から基体を一定の速度で引き上げることにより、潤滑剤層形成用溶液を基体の保護層上の表面に塗布した。潤滑剤層の膜厚は1.4nmとした。<Formation of lubricating layer>
A lubricant was applied on the protective layer using the dip method. That is, the adjusted lubricant layer forming solution is placed in the immersion tank of the dip coating device, the substrate on which each layer up to the protective layer is formed is immersed in the lubricant layer forming solution, and then the substrate from the immersion tank is immersed. The lubricant layer forming solution was applied to the surface on the protective layer of the substrate by pulling up the lubricant layer at a constant rate. The film thickness of the lubricant layer was 1.4 nm.
(実施例2)
窒素雰囲気下、100mLナスフラスコに、本発明のブレンステッド酸としての化合物8 1.57g(Mw1568、1.0mmol)とTHF50mLを仕込み、室温で撹拌し溶解させた。この溶液に本発明のブレンステッド塩基としての化合物11 7.09g(Mw591、12.0mmol)を投入し、室温で1時間、40℃で1時間撹拌した後、溶媒を留去した。残渣をヘプタンのデカンテーションにより、洗浄し、洗液がpH7を示すまで繰り返し上澄みを除去し、本発明の第1の実施形態のフラーレン化合物としての化合物Dを合成した。
化合物Dを用いた以外は、実施例1と同様に、潤滑層を形成し、磁気記録媒体を製造した。(Example 2)
Under a nitrogen atmosphere, 1.57 g (Mw1568, 1.0 mmol) of the compound 8 as Bronsted acid of the present invention and 50 mL of THF were charged in a 100 mL eggplant flask, and the mixture was stirred and dissolved at room temperature. 7.009 g (Mw591, 12.0 mmol) of the
A lubricating layer was formed and a magnetic recording medium was produced in the same manner as in Example 1 except that compound D was used.
(実施例3)
窒素雰囲気下、100mLナスフラスコに、本発明のブレンステッド塩基としての化合物16 (フロンティアカーボン社のJ204)1.25g(Mw1251、1.0mmol)とTHF50mLを仕込み、室温で撹拌し溶解させた。この溶液に本発明のブレンステッド酸としての化合物15 3.37g(Mw562、6.0mmol)を投入し、室温で1時間、40℃で1時間撹拌した後、溶媒を留去した。残渣をヘプタンのデカンテーションにより、洗浄し、洗液がpH7を示すまで繰り返し上澄みを除去し、本発明の第2の実施形態のフラーレン化合物としての化合物Fを合成した。
化合物Fを用いた以外は、実施例1と同様に、潤滑層を形成し、磁気記録媒体を製造した。(Example 3)
In a nitrogen atmosphere, 1.25 g (Mw1251, 1.0 mmol) of compound 16 (J204 of Frontier Carbon Co., Ltd.) as a Bronsted base of the present invention and 50 mL of THF were charged in a 100 mL eggplant flask, and the mixture was stirred and dissolved at room temperature. 15.37 g (Mw562, 6.0 mmol) of the compound as Bronsted acid of the present invention was added to this solution, and the mixture was stirred at room temperature for 1 hour and at 40 ° C. for 1 hour, and then the solvent was distilled off. The residue was washed by decantation of heptane, and the supernatant was repeatedly removed until the washing liquid showed pH 7, and compound F as a fullerene compound of the second embodiment of the present invention was synthesized.
A lubricating layer was formed and a magnetic recording medium was produced in the same manner as in Example 1 except that compound F was used.
(実施例4)
窒素雰囲気下、100mLナスフラスコに、本発明のブレンステッド酸としての化合物6A 1.29g(Mw1291、1.0mmol)とTHF50mL、水50mLを仕込み、室温で撹拌し懸濁させた。この溶液に本発明のブレンステッド塩基としての化合物11 7.09g(Mw591、12.0mmol)を投入し、室温で12時間、40℃で10時間撹拌した後、溶媒を留去した。残渣をヘプタンのデカンテーションにより、洗浄し、洗液がpH7を示すまで繰り返し上澄みを除去し、本発明の第1の実施形態のフラーレン化合物としての化合物Gを合成した。
化合物Gを用いた以外は、実施例1と同様に、潤滑層を形成し、磁気記録媒体を製造した。(Example 4)
Under a nitrogen atmosphere, 1.29 g (Mw1291, 1.0 mmol) of compound 6A as Bronsted acid of the present invention, 50 mL of THF and 50 mL of water were placed in a 100 mL eggplant flask, and the mixture was stirred and suspended at room temperature. 7.009 g (Mw591, 12.0 mmol) of the
A lubricating layer was formed and a magnetic recording medium was produced in the same manner as in Example 1 except that compound G was used.
(比較例1)
Z−DIAC(分子量2000)とオクタデシルアミンとのイオン液体である化合物Hを得た。
化合物Hを用いた以外は、実施例1と同様に、潤滑層を形成し、磁気記録媒体を製造した。 (Comparative Example 1)
Compound H, which is an ionic liquid of Z-DIAC (molecular weight 2000) and octadecylamine, was obtained.
A lubricating layer was formed and a magnetic recording medium was produced in the same manner as in Example 1 except that compound H was used.
(比較例2)
Z−DIAC(分子量2000)と1H,1H,2H,2H−パーフルオロデシルアミンとのイオン液体である化合物Iを得た。
化合物Iを用いた以外は、実施例1と同様に、潤滑層を形成し、磁気記録媒体を製造した。(Comparative Example 2)
Compound I, which is an ionic liquid of Z-DIAC (molecular weight 2000) and 1H, 1H, 2H, 2H-perfluorodecylamine, was obtained.
A lubricating layer was formed and a magnetic recording medium was produced in the same manner as in Example 1 except that Compound I was used.
(フラーレン化合物と潤滑層の評価)
実施例1〜4の化合物B、化合物D、化合物F、化合物G、比較例1および2の化合物Hと化合物I、それらの化合物を含む潤滑層を、後述の評価方法で評価した。評価結果を表3に示す。(Evaluation of fullerene compound and lubricating layer)
The lubricating layer containing Compound B, Compound D, Compound F, Compound G of Examples 1 to 4, Compound H and Compound I of Comparative Examples 1 and 2, and their compounds was evaluated by the evaluation method described later. The evaluation results are shown in Table 3.
[フラーレン化合物の熱分解温度の測定]
TG−DTA(メーカ名:セイコーインスツルメンツ、型番:EXSTAR6000)により、フラーレン化合物について、温度に対する重量減少を測定し、重量減5%における温度を熱分解温度と定義した。測定条件は、昇温速度を10℃/min、Air流量を200mL/minとした。[Measurement of thermal decomposition temperature of fullerene compounds]
The weight loss of the fullerene compound with respect to temperature was measured by TG-DTA (manufacturer name: Seiko Instruments Inc., model number: EXSTAR6000), and the temperature at 5% weight loss was defined as the thermal decomposition temperature. The measurement conditions were a heating rate of 10 ° C./min and an Air flow rate of 200 mL / min.
[潤滑層の摩擦係数の測定]
スライドガラスを基材として潤滑剤をディッピングコーティングし、サンプルを作製した。潤滑剤は、バートレル/エタノール(70/30)を溶媒とし、イオン液体の0.2wt%溶液に調合した。ディッピングコーティングは、潤滑剤槽からスライドガラスを速度50mm/minにて引き上げて行った。[Measurement of friction coefficient of lubricating layer]
A sample was prepared by dipping coating a lubricant on a slide glass as a base material. The lubricant was prepared in a 0.2 wt% solution of an ionic liquid using Bertrel / ethanol (70/30) as a solvent. The dipping coating was performed by pulling the slide glass from the lubricant tank at a speed of 50 mm / min.
自動摩擦測定装置(メーカ名:協和界面化学、型番:TribosterTS−501)を用いて、点接触(3mm鋼球)、重り15g、速度1.7mm/sec、距離20mm、繰り返し回数12回の条件でサンプルの摩擦係数を測定し、12回目の値を表3に記した。 Using an automatic friction measuring device (manufacturer name: Kyowa Surface Chemicals, model number: Triboster TS-501), under the conditions of point contact (3 mm steel ball), weight 15 g, speed 1.7 mm / sec, distance 20 mm, and number of repetitions 12 times. The friction coefficient of the sample was measured, and the 12th value is shown in Table 3.
表3に示すように、実施例1〜4は、合成したフラーレン化合物が300℃以上の熱分解温度を有し、十分な耐熱性を有していることが分かった。
また、実施例1〜4は、熱処理なしで低い摩擦係数が得られるだけでなく、140℃60分、250℃60分の加熱処理を行っても低い摩擦係数が得られた。一方、比較例1〜2は、加熱により摩擦係数が増加した。As shown in Table 3, in Examples 1 to 4, it was found that the synthesized fullerene compound had a thermal decomposition temperature of 300 ° C. or higher and had sufficient heat resistance.
Further, in Examples 1 to 4, not only a low friction coefficient was obtained without heat treatment, but also a low friction coefficient was obtained even after heat treatment at 140 ° C. for 60 minutes and 250 ° C. for 60 minutes. On the other hand, in Comparative Examples 1 and 2, the friction coefficient increased due to heating.
以上のように本発明のフラーレン化合物は、ブレンステッド酸とブレンステッド塩基から形成されるイオン液体であり、前記ブレンステッド酸またはブレンステッド塩基のどちらか一方にフラーレンを有する基を含有し、もう片方にパーフルオロアルキル鎖を含有する。このフラーレンとパーフルオロアルキル鎖をイオン結合で分子化することで、潤滑性と耐熱性が両立できる。 As described above, the fullerene compound of the present invention is an ionic liquid formed from a Bronsted acid and a Bronsted base, and contains a group having a fullerene in either the Bronsted acid or the Bronsted base and the other. Contains a perfluoroalkyl chain. By molecularizing the fullerene and the perfluoroalkyl chain by an ionic bond, both lubricity and heat resistance can be achieved.
1…非磁性基板、2…磁性層、3…保護層、4…潤滑剤層、11…磁気記録媒体 1 ... Non-magnetic substrate, 2 ... Magnetic layer, 3 ... Protective layer, 4 ... Lubricant layer, 11 ... Magnetic recording medium
Claims (10)
前記ブレンステッド酸またはブレンステッド塩基のどちらか一方にフラーレンを有する基を含有し、もう一方にパーフルオロアルキル鎖を含有することを特徴とするフラーレン化合物。
A fullerene compound characterized in that either one of the Bronsted acid or the Bronsted base contains a group having a fullerene, and the other contains a perfluoroalkyl chain.
分子内にフラーレン骨格と、
スルホン酸基またはカルボン酸基と、
を有し、
前記ブレンステッド塩基がパーフルオロポリエーテル鎖を有する
請求項1に記載のフラーレン化合物。The Bronsted acid
With a fullerene skeleton in the molecule,
With a sulfonic acid group or a carboxylic acid group,
Have,
The fullerene compound according to claim 1, wherein the Bronsted base has a perfluoropolyether chain.
分子内にパーフルオロポリエーテル鎖と、
スルホン酸基またはカルボン酸基と、
を有し、
前記ブレンステッド塩基がフラーレン骨格を有する
請求項1に記載のフラーレン化合物。The Bronsted acid
With a perfluoropolyether chain in the molecule,
With a sulfonic acid group or a carboxylic acid group,
Have,
The fullerene compound according to claim 1, wherein the Bronsted base has a fullerene skeleton.
前記ブレンステッド塩基が下記式(10)又は(11)で示される化合物である請求項1又は請求項2に記載のフラーレン化合物。
Cn(OH)x−y(OSO3H)y(6)
(式中、Cnはポリ水酸化フラーレン硫酸水素エステルの母体であるフラーレンを示し、xは10〜30の範囲の数であり、yは5〜10の範囲の数である。CnはC60、C70、C76、C78、C80、C82、C84から選ばれる少なくとも1種である。)
(式中p、qは1〜3である。mは1〜30であり、nは0〜30である。)
CF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2OCH2CH2NH2 (11)The Bronsted acid is a compound represented by the following formula (6), (7) or (8).
The fullerene compound according to claim 1 or 2, wherein the Bronsted base is a compound represented by the following formula (10) or (11).
C n (OH) xy (OSO 3 H) y (6)
(In the formula, C n represents fullerene, which is the base of polyhydroxide fullerene hydrogen sulfate ester, x is a number in the range of 10 to 30, and y is a number in the range of 5 to 10. C n is a number in the range of 5 to 10. At least one selected from 60, C 70 , C 76 , C 78 , C 80 , C 82 , and C 84.)
(In the formula, p and q are 1 to 3, m is 1 to 30, and n is 0 to 30.)
CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 CH 2 OCH 2 CH 2 NH 2 (11)
前記ブレンステッド塩基が下記式(16)で示される化合物である請求項1又は請求項3に記載のフラーレン化合物。
HO3S(CH2)3OCH2CF2−(OCF2CF2)m(OCF2)n−OCF2CH2O(CH2)3SO3H (12)
(式中mは1〜30であり、nは0〜30である。)
CF3CF2CF2CF2−(OCF2CF2)2−OCF2CH2O(CH2)3SO3H (13)
HOOCCF2−(OCF2CF2)m(OCF2)n−OCF2COOH (14)
(式中mは1〜30であり、nは0〜30である。)
CF3CF2CF2CF2−(OCF2CF2)2−OCF2COOH (15)
The fullerene compound according to claim 1 or 3, wherein the Bronsted base is a compound represented by the following formula (16).
HO 3 S (CH 2 ) 3 OCH 2 CF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 CH 2 O (CH 2 ) 3 SO 3 H (12)
(In the formula, m is 1 to 30 and n is 0 to 30.)
CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 CH 2 O (CH 2 ) 3 SO 3 H (13)
HOOCCF 2- (OCF 2 CF 2 ) m (OCF 2 ) n- OCF 2 COOH (14)
(In the formula, m is 1 to 30 and n is 0 to 30.)
CF 3 CF 2 CF 2 CF 2- (OCF 2 CF 2 ) 2- OCF 2 COOH (15)
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